Bothsides Podcast25 Aug 2025

EP 127 | Simon Caulfield: Player–Coach Leadership & Legacy

In this episode, Director of Place Kangaroo Point, Simon Caulfield unpacks how he’s built an office where top performers have their own identities—not “from Simon’s office”—and why the business must thrive without him.

We get into pathways from 500k GCI to seven figures, case studies across high-volume vs high-value models, and Simon’s personal playbook: two champagne COI events a year, a “favorites” list he calls religiously, and being a present, trusted local over flashy ads.

In this Simon shares lessons from moving upmarket (from $555k beginnings to KP’s top end), the difference between selling resi and selling the dream off-the-plan, and the player-coach balance of leading six team presentations a week while still listing and selling.

He dives into Wolfpack Fridays, retaining top talent by giving them reasons to stay, using an AI recorder to capture meetings and train staff, and the three-corner support team (manager, coach, trainer). Above all: listen intently, play to your strengths, move the needle each year, and leave people in a better place than you found them.

Topics covered:

Building a business where agents thrive under their own brands
Leadership mindset: “Leave people in a better place”
Pathways from 500k to $1M+ GCI and choosing the right model
Case studies: high-value vs high-volume strategies
Simon’s COI playbook: champagne events & “diamond” call list
Moving upmarket: perception, results, and social proof
Resi vs off-the-plan: selling the dream before it exists
Player–coach leadership and when to step back from listing
Wolfpack Fridays: training, collaboration, and shared challenges
Retaining top talent with support, recognition, and care
Practical AI for onboarding and process improvement

Legacy: success measured by impact, not trophies

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Thank you so much for listening!

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